Literature DB >> 30478935

Ligand-Promoted Non-Directed C-H Cyanation of Arenes.

Luo-Yan Liu1, Kap-Sun Yeung2, Jin-Quan Yu1.   

Abstract

This article reports the first example of a 2-pyridone accelerated non-directed C-H cyanation with an arene as the limiting reagent. This protocol is compatible with a broad scope of arenes, including advanced intermediates, drug molecules, and natural products. A kinetic isotope experiment (kH /kD =4.40) indicates that the C-H bond cleavage is the rate-limiting step. Also, the reaction is readily scalable, further showcasing the synthetic utility of this method.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  2-pyridone; C−H activation; arenes; cyanation; palladium

Year:  2019        PMID: 30478935      PMCID: PMC6599606          DOI: 10.1002/chem.201805772

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  7 in total

1.  meta C-H Arylation of Electron-Rich Arenes: Reversing the Conventional Site Selectivity.

Authors:  Luo-Yan Liu; Jennifer X Qiao; Kap-Sun Yeung; William R Ewing; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2019-09-06       Impact factor: 15.419

2.  meta-Selective C-H Arylation of Fluoroarenes and Simple Arenes.

Authors:  Luo-Yan Liu; Jennifer X Qiao; Kap-Sun Yeung; William R Ewing; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2020-07-09       Impact factor: 15.336

Review 3.  Advancing the Logic of Chemical Synthesis: C-H Activation as Strategic and Tactical Disconnections for C-C Bond Construction.

Authors:  Nelson Y S Lam; Kevin Wu; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2021-02-04       Impact factor: 16.823

4.  Palladium(II)-Catalyzed Selective Arylation of Tertiary C-H Bonds of Cyclobutylmethyl Ketones Using Transient Directing Groups.

Authors:  Jin-Tang Cheng; Li-Jun Xiao; Shao-Qun Qian; Zhe Zhuang; An Liu; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2022-03-09       Impact factor: 16.823

5.  S,O-Ligand Promoted meta-C-H Arylation of Anisole Derivatives via Palladium/Norbornene Catalysis.

Authors:  Verena Sukowski; Manuela van Borselen; Simon Mathew; M Ángeles Fernández-Ibáñez
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-21       Impact factor: 16.823

6.  Facile synthesis of 6-organyl-4-(trifluoromethyl)pyridin-2(1H)-ones and their polyfluoroalkyl-containing analogs.

Authors:  S O Kushch; M V Goryaeva; Ya V Burgart; G A Triandafilova; K O Malysheva; O P Krasnykh; N A Gerasimova; N P Evstigneeva; V I Saloutin
Journal:  Russ Chem Bull       Date:  2022-09-23       Impact factor: 1.704

7.  Palladium-Catalyzed Nondirected Late-Stage C-H Deuteration of Arenes.

Authors:  Mirxan Farizyan; Arup Mondal; Sourjya Mal; Fritz Deufel; Manuel van Gemmeren
Journal:  J Am Chem Soc       Date:  2021-09-28       Impact factor: 15.419

  7 in total

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